luxury property with terrace for sale East Chatham, United States

Nestled in the picturesque Berkshires, this historic circa-1776 Richmond estate seamlessly blends Colonial charm, timeless elegance, and premier equestrian amenities. The expansive compound features a beautifully maintained seven-bedroom, 7.5-bath main residence/Inn, three guest cottages, multiple barns, and a spacious entertaining barn. The distinguished main home offers a gracious dining room, entrance parlor, stately library, cozy den, period greenhouse, and well-appointed kitchen. An equestrian enthusiast's dream, the property boasts lush paddocks, multiple barns, a 6,000-square-foot heated indoor riding arena with viewing area and owner's apartment, and a professional outdoor riding ring, providing exceptional facilities for year-round training and entertaining.

Down a long, private drive lined with mature maple trees, a remarkable piece of Hudson Valley history awaits. Set within luxurious privacy yet just a pleasant walk from the heart of Kinderhook, this extraordinary antique Dutch Colonial offers the rare combination of architectural authenticity, refined modern comforts, and effortless access to one of the region’s most charming villages. Public records date the home to 1840, though references to its origins reaching back to the early 1700s add another layer to its already fascinating history. For those who appreciate early American architecture, homes with this degree of original character are increasingly difficult to find. From the moment you enter through the classic double-hung Dutch door, your foot meets the aged wide-plank floors of the foyer and the feeling is immediate: this is a home with stories to tell. Two grandly proportioned parlors flank the entry, each anchored by an impressive brick fireplace. To the right, the formal living room provides an intimate setting for receiving guests and lingering conversation; to the left, a handsome study offers a quieter retreat. Both spaces have been thoughtfully restored, preserving their original architectural integrity while creating rooms that feel warm, elegant, and entirely livable today. Beyond, a luminous atrium dining corridor draws you toward the informal dining room and breakfast nook, ultimately opening into a spectacular gourmet kitchen. Oversized top-of-the-line appliances, generous custom cabinetry, and another enormous brick fireplace make this the natural gathering place of the house. Framed views extend beyond the kitchen and dining spaces toward a pond and beautifully manicured English-style gardens, bringing the landscape into everyday life. A separate formal dining room just off the kitchen sets the stage for memorable dinners and long evenings with friends and family. Upstairs, five generously proportioned bedrooms each possess their own distinct personality while continuing the architectural language found throughout the home: original details, deep-set windows, aged floors, and the unmistakable sense of permanence that only an antique house can provide. Beautifully designed bathrooms introduce a sophisticated modern counterpoint, including a luxurious steam shower designed for unwinding at the end of the day. Across the property, privately tucked to the side, is an expansive in-ground pool accompanied by a charming two-bedroom, two-bath pool house. Designed as its own private retreat, the guest house allows friends and family to settle in comfortably while the main house remains wonderfully serene. Together, the pool and pool house create an idyllic setting for long summer afternoons, impromptu dinners, and weekends that seem to stretch a little longer than expected. And then there is Kinderhook itself. Just a walk from the property, the village offers a wonderfully curated collection of shops, cafés, restaurants, and a wine bar—places with the sophistication and sense of discovery found in the Hudson Valley’s better-known destinations, but without the weekend crowds. It is precisely the kind of place that feels discovered rather than descended upon. A home of extraordinary provenance, privacy, and presence, this is an uncommon opportunity to own a piece of the Hudson Valley’s architectural history while enjoying the pleasures of contemporary country living. Historic at heart, beautifully evolved, and perfectly positioned in Kinderhook

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody and Stearns, this Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

Rare, renovated Berkshire investment compound on 0.59 acres in pedestrian-friendly Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Moments from Berkshire Mountain Bakery; minutes to downtown Great Barrington and Tanglewood. A rare, turnkey find!

A modern country home inspired by the farmhouses of the Hudson Valley. Taconic Creek Road is tucked away amongst rolling hills and large surrounding parcels, on a beautiful dead end road with just a few lovely houses. The palette is restrained but luxurious with a thoughtful layout and custom design details. Spanning 2,100 square feet, you’ll find lime washed walls with stunning depth of color, custom millwork and wideboard wood flooring that adds warmth to the space. The main living area is anchored by the open kitchen, with Tundra Gray marble counters, an English farmhouse sink, custom inset cabinetry and paneled appliances. A deVOL pendant hangs over the kitchen table. The sitting area is lined with custom built bookshelves and there are large, deep windows lining the room. They face out into the garden, and french doors at the center take you onto the patio. There is storage and a built in bench at the entry for your boots and bags, and a lovely bath on the main level with Noguchi pendant lights. Upstairs, a light filled sitting room walks out to a screened in porch, and there are three bedrooms spread out across the floor. The primary suite is large with a stunning picture window, an office/walk-in closet and a gorgeous bathroom. You’ll find a walk-in-shower and soaking tub with views of the surrounding treetops. Two other bedrooms share the third bathroom off the hall. There is an extensive list of upgrades that includes a new roof, HVAC and septic, and the current owners buried the electrical lines to the house. A large pool is surrounded by lilacs and hedges, private and peaceful, and there is a garage for parking. Taconic Creek Road offers a rare level of calm and sophistication just 15m to Hudson and Amtrak and under 2.5h north of NYC.

Newly completed and set on 11.7 private acres in the heart of Hillsdale, this architect-designed 4-bedroom, 4-bath modernist residence combines striking contemporary architecture with sweeping pastoral and mountain views in every direction. Arriving via a long private driveway, rolling lawns and open fields unfold toward a home defined by bold geometric forms, expansive walls of glass, and a seamless connection to the surrounding landscape. Just minutes from the Hamlet of Hillsdale, Catamount Mountain Resort, Great Barrington, and Hudson, the property offers a rare balance of architectural refinement, privacy, and access to the region’s most desirable destinations. The residence is centered around a dramatic great room with a soaring 20-foot vaulted ceiling and a wood-burning fireplace clad in richly toned chestnut marble. Floor-to-ceiling glass and oversized Arcadia sliding doors dissolve the boundary between interior and exterior, opening onto more than 540 square feet of covered outdoor living space designed for year-round entertaining and relaxed outdoor living. Throughout the home, natural light shifts across clean architectural lines and warm materiality, reinforcing a strong connection between structure and landscape. The kitchen serves as both a design centerpiece and functional workspace, featuring custom walnut cabinetry crafted by a Brooklyn cabinetmaker, integrated Fisher & Paykel and Bosch appliances, an oversized monolithic island, and a 48-inch double-oven gas range. A fully equipped butler’s pantry and bar area provides additional prep space, storage, second dishwasher, and additional refrigeration, allowing the main kitchen to remain clean and open for entertaining. The primary suite is a private retreat with vaulted ceilings, a custom dressing room, and a spa-like bath finished in dramatic Calacatta Violetta marble, featuring a soaking tub, oversized shower, and fluted glass steel-framed doors. Upstairs, a second ensuite bedroom offers its own walk-in closet and marble-appointed bath, complemented by an additional guest bedroom suite. A versatile fourth bedroom on the main level provides flexible use as a guest suite, office, media room, or wellness space with direct access to the outdoor terrace. Designed for high-performance modern living, the home includes spray foam insulation, high-performance windows, forced-air heating and central air conditioning, on-demand hot water, Lutron lighting controls, remote-access thermostats, generator hookup readiness, and a detached heated 26' x 26' two-car garage. Located just minutes from Catamount Mountain Resort and within easy reach of Great Barrington and Hudson, the home places owners at the center of the Hudson Valley and Berkshires lifestyle. Days might begin with coffee overlooking the fields, followed by a visit to the Saturday farmers market, skiing at Catamount, or hiking nearby trails. Afternoons can be spent browsing Hudson’s celebrated design and antique shops or exploring the galleries, bookstores, and restaurants of Great Barrington. Evenings bring performances at local theaters and live music venues, or a quiet return home as the light settles across the landscape. The setting balances architectural refinement, outdoor recreation, and cultural depth in equal measure. A rare expression of contemporary Hudson Valley living, where architecture, light, and landscape are held in perfect balance. An adjoining 6.73-acre parcel is also available for purchase, offering the opportunity to expand the estate or create a private family compound. (listing agent has a financial interest in the property)

Overlooking ten acres of city-owned green space, this passive house is just two blocks from the best restaurants and shops that Hudson has to offer but a world away. The site is entirely unique within Hudson, the terraced yard is exceptionally private and overlooks pastoral fields, and a small waterfall out back can be heard from the house. The backyard is enveloped by trees, this is one of a few in-town locations where you'll find no neighbors in sight. Built c2015, the incredibly efficient home has 3 bedrooms and 2 full baths spread out over two stories. The main living space is an open kitchen and living room, both walk out onto the deck where one can enjoy the outdoors right in Hudson proper. On the lower level you’ll find radiant concrete floors. The home is clad in COR-TEN steel siding and the European windows are triple-pane. Outside, stone walls terrace the yard, there is a built-in grill/firepit, a large storage shed and off-street parking. This incredibly unique location offers in-town convenience and proximity to nature— it is truly the best of both worlds.

Versatile mixed-use property pairing a sophisticated second-floor apartment with a flexible first-floor residence that doubles as an ideal commercial or gallery space. Overlooking a tranquil year-round brook and a private backyard, the offering sits right downtown Egremont and includes the convenience of an ample garage. | Property Highlights | Second-Floor Apartment: Sophisticated, charming living quarters featuring high-quality finishes, total privacy, and serene views of the brook and grounds. First-Floor Mixed-Use Space: Currently configured as a comfortable residential apartment while offering incredible potential for an art gallery, retail boutique, or commercial enterprise. Ample Garage: Generous garage space providing excellent storage, parking, or workshop potential. Exceptional Septic Infrastructure: Robustly engineered system designed to service a 35-seat restaurant. First floor has been a restaurant, bookshop, and now a residence.